US4501890AExpiredUtility

Trans-(±)-2,4,6-substituted-5,5a,6,7,8,9,9a,10-octahydro-pyrimido[4,5-g]quinolines

Assignee: LILLY CO ELIPriority: Sep 26, 1983Filed: Sep 26, 1983Granted: Feb 26, 1985

Est. expirySep 26, 2003(expired)· nominal 20-yr term from priority

Inventors:Cynthia L. Nichols Edmund C. Kornfeld

C07D 471/04A61P 9/12C07D 215/20

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Claims

Abstract

Trans-(+/-)-2-Amino or substituted amino-4-permissibly-substituted 6-lower alkyl or allyl-5,5a,-6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinolines, the corresponding trans-(-)-stereoisomers and salts thereof, useful in treating anxiety, Parkinson's Syndrome, sexual dysfunction, depression, hypertension and elevated prolactin levels, and intermediates useful for the synthesis thereof.

Claims

exact text as granted — not AI-modified

We claim: 
     
       1. A trans-(±)-2,4,6-permissibly substituted octahydropyrimido[4,5-g]quinoline of the formula: ##STR20## wherein R is H, CN, C 1-3  alkyl O--CO, C 1-3  alkyl or allyl; R 1  is NH 2 , NHR 3 , NR 4  R 5 , R 2  is H, CH 3 , Cl or Br; R 3  is methyl, ethyl or n-propyl, C 1-3  alkyl-CO, phenyl-CO or substituted phenyl-CO, wherein said substituents are 1 or 2 members of the group: chloro, fluoro, bromo, methyl, ethyl, methoxy, ethoxy and trifluoromethyl; R 4  and R 5  are individually methyl, ethyl or n-propyl; and pharmaceutically acceptable acid addition salts thereof. 
     
     
       2. A trans-(-)-2,4,6-permissibly substituted octahydropyrimido[4,5-g]quinoline of the formula ##STR21## wherein R is H, CN, C 1-3  alkyl O--CO, C 1-3  alkyl or allyl; R 1  is NH 2 , NHR 3 , NR 4  R 5 , R 2  is H, CH 3 , Cl or Br, R 3  is methyl, ethyl or n-propyl, C 1-3  alkyl-CO, phenyl-CO or substituted phenyl-CO, wherein said substituents are 1 or 2 members of the group: chloro, fluoro, bromo, methyl, ethyl, methoxy, ethoxy and trifluoromethyl; R 4  and R 5  are individually methyl, ethyl or n-propyl; and pharmaceutically acceptable acid addition salts thereof. 
     
     
       3. A compound according to claim 1 in which R is methyl, ethyl, n-propyl or allyl, R 1  is amino or acetamino and R 2  is H or Cl. 
     
     
       4. A compound according to claim 2 in which R is methyl, ethyl or n-propyl, R 1  is NH 2  or acetamino, and R 2  is H or Cl. 
     
     
       5. A compound of the formula ##STR22## in which R 1  is NH 2 , NHCH 3 , N(CH 3 ) 2 , NH--CO--CH 3  or NH--CO--phenyl, R 2  is H, Cl, Br or CH 3  and R 6  is C 1-3  alkyl or allyl. 
     
     
       6. A compound according to claim 5 in which R 1  is NH 2  or NH--CO--CH 3 , R 2  is H or Cl and R 6  is n-propyl, and pharmaceutically-acceptable salts thereof. 
     
     
       7. A compound according to claim 2 in which R is C 1-3  alkyl or allyl. 
     
     
       8. A compound according to claim 2 in which R 2  is H. 
     
     
       9. A compound according to claim 2 in which R 1  is NH 2 . 
     
     
       10. A compound according to claim 2 in which R is n-propyl. 
     
     
       11. A compound according to claim 1 in which R is C 1-3  alkyl or allyl. 
     
     
       12. A compound according to claim 1 in which R 2  is H. 
     
     
       13. A compound according to claim 1 in which R 1  is NH 2 . 
     
     
       14. A compound according to claim 1 in which R is n-propyl. 
     
     
       15. A compound according to claim 1 in which R is CN, C 1-3  alkyl O--CO or H, R 1  is NH 2  and R 2  is CH 3 , Cl, Br or H. 
     
     
       16. A hydrochloride salt of a compound according to claim 1. 
     
     
       17. A compound according to claim 1, said compound being trans-(±)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-c]quinoline. 
     
     
       18. A compound according to claim 2, said compound being trans-(-)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       19. A compound according to claim 1, said compound being trans-(±)-2-acetamino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       20. A compound according to claim 1, said compound being trans-(±)-2-amino-4-chloro-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       21. A hydrochloride salt of a compound according to claim 2. 
     
     
       22. A salt according to claim 16, said salt being trans-(-)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline dihydrochloride. 
     
     
       23. A compound according to claim 15, said compound being trans-(±)-2-amino-6-cyano-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       24. A compound according to claim 15, said compound being trans-(±)-2-amino-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       25. A compound according to claim 2 in which R is CN, C 1-3  alkyl O--CO or H, R 1  is NH 2  and R 2  is CH 3 , Cl, Br or H. 
     
     
       26. A compound according to claim 25, said compound being trans-(-)-2-amino-6-cyano-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       27. A compound according to claim 25, said compound being trans-(-)-2-amino-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline. 
     
     
       28. A pharmaceutical formulation in unit dosage form adapted for administration to counter depression, alleviate anxiety, reduce elevated blood pressure, lower excessively high prolactin levels, or treat Parkinson&#39;s Syndrome comprising per dosage unit, a standard pharmaceutical excipient plus an amount of a drug according to claim 5 to inhibit the secretion of prolactin levels, to relieve anxiety, to counter depression, to lower blood pressure of hypertensives or to treat Parkinson&#39;s Syndrome. 
     
     
       29. A formulation according to claim 28 in which trans-(-)-2-amino-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline dihydrochloride is the active drug.

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